2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶的最终形式与2'-脱氧鸟苷及其磷酸酯在体外反应时鸟嘌呤C-8处加合物的形成。
Adduct formation at C-8 of guanine on in vitro reaction of the ultimate form of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine with 2'-deoxyguanosine and its phosphate esters.
作者信息
Nagaoka H, Wakabayashi K, Kim S B, Kim I S, Tanaka Y, Ochiai M, Tada A, Nukaya H, Sugimura T, Nagao M
机构信息
Carcinogenesis Division, National Cancer Center Research Institute, Tokyo.
出版信息
Jpn J Cancer Res. 1992 Oct;83(10):1025-9. doi: 10.1111/j.1349-7006.1992.tb02716.x.
Abstract
We examined the reactivity of the N-hydroxyamino derivative of a carcinogenic heterocyclic amine, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), after its O-acetylation with four 2'-deoxyribonucleoside 3'-monophosphates. 32P-Postlabeling analysis demonstrated that the levels of adducts with 2'-deoxyguanosine 3'-monophosphate were much higher than those with the other three nucleotides. 1H-NMR, mass spectral and UV absorption spectral analyses of the major adducts formed by N-acetyoxy-PhIP with 2'-deoxyguanosine and with its phosphate esters indicated that PhIP bound at the C-8 position of guanine, as previously demonstrated with other heterocyclic amines.
摘要
我们检测了致癌杂环胺2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶（PhIP）的N-羟基氨基衍生物与四种2'-脱氧核糖核苷3'-单磷酸进行O-乙酰化反应后的反应活性。32P后标记分析表明，2'-脱氧鸟苷3'-单磷酸加合物的水平远高于其他三种核苷酸的加合物水平。对N-乙酰氧基-PhIP与2'-脱氧鸟苷及其磷酸酯形成的主要加合物进行的1H-核磁共振、质谱和紫外吸收光谱分析表明，PhIP与鸟嘌呤的C-8位结合，这与之前对其他杂环胺的研究结果一致。
相似文献
1
Adduct formation at C-8 of guanine on in vitro reaction of the ultimate form of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine with 2'-deoxyguanosine and its phosphate esters.2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶的最终形式与2'-脱氧鸟苷及其磷酸酯在体外反应时鸟嘌呤C-8处加合物的形成。
Jpn J Cancer Res. 1992 Oct;83(10):1025-9. doi: 10.1111/j.1349-7006.1992.tb02716.x.
2
Detection of guanine-C8-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine adduct as a single spot on thin-layer chromatography by modification of the 32P-postlabeling method.通过改进的32P后标记法在薄层色谱上以单个斑点形式检测鸟嘌呤-C8-2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶加合物
Jpn J Cancer Res. 1994 Feb;85(2):113-7. doi: 10.1111/j.1349-7006.1994.tb02068.x.
3
Improved high-performance liquid chromatography analysis of 32P-postlabeled 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-DNA adducts using in-line precolumn purification.采用在线柱前纯化改进32P后标记的2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶-DNA加合物的高效液相色谱分析。
J Chromatogr B Biomed Appl. 1996 Apr 26;679(1-2):91-101. doi: 10.1016/0378-4347(96)00010-2.
5
Identification of N-(Deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA.鉴定N-（8-脱氧鸟苷基）-2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶为食源性致癌物2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶与DNA形成的主要加合物。
Chem Res Toxicol. 1992 Sep-Oct;5(5):691-7. doi: 10.1021/tx00029a016.
6
32-P-HPLC analysis of DNA adducts formed in vitro and in vivo by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline, utilizing an improved adduct enrichment procedure.利用改进的加合物富集程序，对2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶和2-氨基-3,4,8-三甲基-3H-咪唑并[4,5-f]喹喔啉在体外和体内形成的DNA加合物进行32-P-HPLC分析。
Chem Res Toxicol. 1996 Sep;9(6):1050-6. doi: 10.1021/tx960050a.
7
Synthesis and spectroscopic characterization of site-specific 2-amino-1-methyl-6-phenylimidazo.位点特异性2-氨基-1-甲基-6-苯基咪唑的合成与光谱表征
Nucleic Acids Res. 2001 May 1;29(9):1951-9. doi: 10.1093/nar/29.9.1951.
8
Synthesis of the PhIP adduct of 2'-deoxyguanosine and its incorporation into oligomeric DNA.2'-脱氧鸟苷的PhIP加合物的合成及其掺入寡聚DNA中。
Chem Res Toxicol. 2006 Jun;19(6):734-8. doi: 10.1021/tx0600191.
9
Synthesis and 32P-postlabeling/high-performance liquid chromatography separation of diastereomeric 1,N2-(1,3-propano)-2'-deoxyguanosine 3'-phosphate adducts formed from 4-hydroxy-2-nonenal.由4-羟基-2-壬烯醛形成的非对映体1,N2-(1,3-丙基)-2'-脱氧鸟苷3'-磷酸加合物的合成及32P后标记/高效液相色谱分离
Chem Res Toxicol. 1997 Nov;10(11):1259-65. doi: 10.1021/tx970100r.
10
Mass Spectrometric Characterization of Human Serum Albumin Adducts Formed with N-Oxidized Metabolites of 2-Amino-1-methylphenylimidazo[4,5-b]pyridine in Human Plasma and Hepatocytes.人血浆和肝细胞中2-氨基-1-甲基苯基咪唑并[4,5-b]吡啶的N-氧化代谢产物与人血清白蛋白加合物的质谱表征
Chem Res Toxicol. 2015 May 18;28(5):1045-59. doi: 10.1021/acs.chemrestox.5b00075. Epub 2015 Apr 10.
引用本文的文献
1
First report on a series of food-derived mutagenic and carcinogenic heterocyclic amines.关于一系列食物来源的诱变和致癌杂环胺的首次报告。
Proc Jpn Acad Ser B Phys Biol Sci. 2024;100(10):545-557. doi: 10.2183/pjab.100.033.
2
Association between NAT2, CYP1A1, and CYP1A2 genotypes, heterocyclic aromatic amines, and prostate cancer risk: a case control study in Japan.N-乙酰基转移酶2（NAT2）、细胞色素P450 1A1（CYP1A1）和细胞色素P450 1A2（CYP1A2）基因多态性、杂环胺与前列腺癌风险之间的关联：日本的一项病例对照研究
Environ Health Prev Med. 2017 Oct 24;22(1):72. doi: 10.1186/s12199-017-0681-0.
3
Base-Displaced Intercalated Conformation of the 2-Amino-3-methylimidazo[4,5-f]quinoline N(2)-dG DNA Adduct Positioned at the Nonreiterated G(1) in the NarI Restriction Site.位于NarI限制位点非重复G(1)处的2-氨基-3-甲基咪唑并[4,5-f]喹啉N(2)-dG DNA加合物的碱基置换插入构象。
Chem Res Toxicol. 2015 Jul 20;28(7):1455-68. doi: 10.1021/acs.chemrestox.5b00140. Epub 2015 Jun 17.
4
Base-displaced intercalation of the 2-amino-3-methylimidazo[4,5-f]quinolone N2-dG adduct in the NarI DNA recognition sequence.碱基位移插入 Narl 识别序列中 2-氨基-3-甲基咪唑[4,5-f]喹啉 N2-dG 加合物。
Nucleic Acids Res. 2014 Mar;42(5):3450-63. doi: 10.1093/nar/gkt1109. Epub 2013 Dec 23.
5
Detection of endogenous DNA adducts, O-carboxymethyl-2'-deoxyguanosine and 3-ethanesulfonic acid-2'-deoxycytidine, in the rat stomach after duodenal reflux.十二指肠反流后大鼠胃内内源性DNA加合物、O-羧甲基-2'-脱氧鸟苷和3-乙磺酸-2'-脱氧胞苷的检测。
Cancer Sci. 2008 Sep;99(9):1741-6. doi: 10.1111/j.1349-7006.2008.00871.x. Epub 2008 Jun 28.
6
DNA sequence modulates the conformation of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme.DNA序列在NarI限制酶的识别序列中调节食物诱变剂2-氨基-3-甲基咪唑并[4,5-f]喹啉的构象。
Biochemistry. 2007 Jul 24;46(29):8498-516. doi: 10.1021/bi700361u. Epub 2007 Jun 30.
7
Grilled meat consumption and PhIP-DNA adducts in prostate carcinogenesis.烤肉消费与前列腺癌发生过程中的PhIP-DNA加合物
Cancer Epidemiol Biomarkers Prev. 2007 Apr;16(4):803-8. doi: 10.1158/1055-9965.EPI-06-0973.
8
Base-displaced intercalated structure of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme, a hotspot for -2 bp deletions.食品诱变剂2-氨基-3-甲基咪唑[4,5-f]喹啉在NarI限制酶识别序列中的碱基置换插入结构，即-2bp缺失的热点区域。
J Am Chem Soc. 2006 Aug 9;128(31):10085-95. doi: 10.1021/ja062004v.
9
Heterocyclic amines: Mutagens/carcinogens produced during cooking of meat and fish.杂环胺：肉类和鱼类烹饪过程中产生的诱变剂/致癌物。
Cancer Sci. 2004 Apr;95(4):290-9. doi: 10.1111/j.1349-7006.2004.tb03205.x.
10
More frequent beta-catenin gene mutations in adenomas than in aberrant crypt foci or adenocarcinomas in the large intestines of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-treated rats.在2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶（PhIP）处理的大鼠大肠中，腺瘤中β-连环蛋白基因突变比异常隐窝灶或腺癌更频繁。
Jpn J Cancer Res. 2000 Aug;91(8):792-6. doi: 10.1111/j.1349-7006.2000.tb01015.x.
本文引用的文献
1
Activation of a mutagen, 3-amino-1-methyl-5H-pyrido[4,3-b]indole. Identification of 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole and its reacion with DNA.诱变剂3-氨基-1-甲基-5H-吡啶并[4,3-b]吲哚的激活。3-羟基氨基-1-甲基-5H-吡啶并[4,3-b]吲哚的鉴定及其与DNA的反应。
Biochem Biophys Res Commun. 1980 Sep 16;96(1):355-62. doi: 10.1016/0006-291x(80)91222-x.
2
The isolation and identification of a new mutagen from fried ground beef: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).从煎牛肉末中分离和鉴定一种新的诱变剂：2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶（PhIP）。
Carcinogenesis. 1986 Jul;7(7):1081-6. doi: 10.1093/carcin/7.7.1081.
3
Reaction of N-hydroxylamine and N-acetoxy derivatives of 2-amino-3-methylimidazolo[4,5-f]quinoline with DNA. Synthesis and identification of N-(deoxyguanosin-8-yl)-IQ.2-氨基-3-甲基咪唑并[4,5-f]喹啉的N-羟基胺和N-乙酰氧基衍生物与DNA的反应。N-(脱氧鸟苷-8-基)-IQ的合成与鉴定。
Carcinogenesis. 1988 Jun;9(6):1061-5. doi: 10.1093/carcin/9.6.1061.
4
Studies on environmental chemical carcinogenesis in Japan.日本环境化学致癌作用的研究。
Science. 1986 Jul 18;233(4761):312-8. doi: 10.1126/science.3088728.
5
New environmental carcinogens in daily life.日常生活中的新型环境致癌物。
Trends Pharmacol Sci. 1988 Jun;9(6):205-9. doi: 10.1016/0165-6147(88)90086-7.
6
Induction of lymphoma in CDF1 mice by the food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.食物诱变剂2-氨基-1-甲基-6-苯基咪唑[4,5-b]吡啶诱导CDF1小鼠淋巴瘤的发生。
Jpn J Cancer Res. 1989 Dec;80(12):1176-8. doi: 10.1111/j.1349-7006.1989.tb01651.x.
7
DNA modification by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rats.大鼠中2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶对DNA的修饰作用
Jpn J Cancer Res. 1989 Dec;80(12):1145-8. doi: 10.1111/j.1349-7006.1989.tb01644.x.
8
Differential rates of metabolic activation and detoxication of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by different cytochrome P450 enzymes.
Carcinogenesis. 1990 Mar;11(3):489-92. doi: 10.1093/carcin/11.3.489.
9
Role of sulfation and acetylation in the activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine to intermediates which bind DNA.硫酸化和乙酰化在将2-羟基氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶激活为与DNA结合的中间体中的作用。
Mutat Res. 1990 Nov;245(3):185-90. doi: 10.1016/0165-7992(90)90048-o.
10
Induction of intestinal adenocarcinomas by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Nagase analbuminemic rats.2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶在长谷川无白蛋白血症大鼠中诱发肠腺癌
Jpn J Cancer Res. 1991 Apr;82(4):363-6. doi: 10.1111/j.1349-7006.1991.tb01855.x.
Zotero 插件